CN107325147A - The screening technique of fulvoushair honeysuckle flower moderate resistance hypertensin conversion enzyme activity composition - Google Patents
The screening technique of fulvoushair honeysuckle flower moderate resistance hypertensin conversion enzyme activity composition Download PDFInfo
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- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
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- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
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- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
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- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
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Abstract
The invention discloses a kind of screening technique of fulvoushair honeysuckle flower moderate resistance hypertensin conversion enzyme activity composition, fulvoushair honeysuckle flower is crushed, alcohol reflux extracts 3 merging extract solutions, reclaim ethanol to without alcohol taste；Extracted with chloroform；Through silica gel column chromatography, with chloroform methanol (100:1~1:1) gradient elution, is instructed to merge same composition with silica gel thin-layer chromatography, obtains flow point 1~17；Active testing is carried out respectively；The good flow point of selection activity, through silica gel column chromatography, with chloroform methanol (60:1~8:1) gradient elution, then through the gel column chromatographies of Sephadex LH 20, with chloroform methanol (1:1~0:1) it is eluent；Filter out cypress biflavone and apiolin with high activity.
Description
Technical field
The invention belongs to fulvoushair honeysuckle flower chemical constitution study technical field, it is related to anti-angiogenic tight in a kind of fulvoushair honeysuckle flower
Open the screening technique of plain invertase activity composition.
Background technology
Chinese herbal medicine is the rarity of human civilization, and irreplaceable effect is played in physianthropy history.Due to nothing
Pollution, it is nuisanceless, the characteristics of high-efficiency low-toxicity, favored by common people.Many experiments show Chinese herbal medicine to painstaking effort such as treatment hypertension
Pipe disease has good effect.The effective Chinese medicine of hypotensive is a lot, such as yncaria stem with hooks, the root of kudzu vine, chrysanthemum indicum, selfheal, according to system
In respect of kind more than 100.Therefore ACEI is screened from Chinese herbal medicine significant, can is not only the new ACEI hypotensor things of exploitation
Some previous works are done, the Hypotensive Mechanism of Chinese herbal medicine can also be inquired into from the angle for suppressing ACE activity.Since nineteen sixty-five Ferria
Et al. find natural A CEI first from the pit viper venom of South America since, numerous studies find ACEI be widely present in natural products
In.Natural A CEI has advantages below compared with synthesizing ACEI：(1) it is safe.Due to being with food and gentle crude drug
Thing is raw material, therefore human body will not be damaged.(2) antihypertensive effect is gentle, single-minded, lasting.Natural A CEl only can be to high blood
Pressure patient has antihypertensive effect, and normal person's blood pressure is not influenceed.(3) have no side effect.There is secondary work clinical decompression class medicine at present more
With, and yet there are no the report of natural A CEI side effects.ACEI is found from natural resources, it has also become the weight of domestic and foreign scholars research
Want problem.
The ACEI obtained at present from natural resources mainly has three major types, comes from peptide matters, the You Jiduo of food proteins
Phenolic acid and flavanol compound material and alkaloids substance.Wherein by the most common, the scientific research that digests the report of ACE Antihypertensive Peptides
Persons are found that largely from the zymolyte of insect, animal, plant, dairy produce and marine protein has ACEI activity
Small peptide.In addition to ace inhibitory peptide, organic polyphenol acids and flavanol compound material are also more to ACE inhibitory activity report.Such as me
General flavone compound-the flavone acetylsalicylate extracted in the Nian Qiancong plant sea-buckthorns of state more than 20, has been used for clinic, and research shows to reduce
Endothelin, elevation of NO, the activity and Ang II for suppressing ACE is generated and is depressured.Actis-Goretta groups test result indicates that, it is rich
Material containing flavanols, such as red wine, white wine, tea and chocolate are to the active inhibited of ACE.Ottaviani et al.
Dimer, tetramer and the hexamer for measuring anthocyanidin are respectively 97.0,4.4 and 8.2mM to the IC50 values of ACE inhibitory activity.
Loizzo etc. is found that 6 chromocor compounds with ACE inhibitory activity from the high tree of heaven of Chinese medicine.High small equality people is water-soluble from the red sage root
Property extracting section goes out the tanshin polyphenolic acid B with ACE inhibitory activity.It is less to the report of ACE inhibitory action about alkaloids substance,
Kang et al. has found that fritillaria extract has inhibitory action to ACE, wherein peiminine, peimine and peimisine for activity into
Point.
Lonicera is the type genus of Caprifoliaceae, about 200 kinds of the whole world, and China has 98 kinds, is widely distributed in each provinces and regions.Have not in category
Few medicinal plant, such as honeysuckle is famous Chinese medicine with a long history, and the bud of this platymiscium is used as flos lonicerae material commodity
There are about 18 kinds.Because the platymiscium has a variety of physiologically actives and widely distributed, for a long time, the chemical composition of woodbine
Turn into one of focus of research with bioactivity.
Fulvoushair honeysuckle flower is Caprifoliaceae woodbine, has effects that clearing heat and detoxicating, dispelling wind and heat from the body, for too fat to move malignant boil
Sore, larynx numbness, erysipelas, toxic-heat and blood stasis, anemopyretic cold.
At present, both at home and abroad to fulvoushair honeysuckle flower chemical composition and pharmacology activity research report is less.Our Primary Studies
It was found that, the chloroform extraction part of the ethanol extract of fulvoushair honeysuckle flower 90% shows stronger to angiotensin converting enzyme (ACE)
Inhibitory activity.Further experiment shows that fulvoushair honeysuckle flower contains the chemical compositions such as flavonoids, triterpenes, sequiterpene and phenolic acid class,
And therefrom obtain multiple monomeric compounds.In order to illustrate the ACEI active components of fulvoushair honeysuckle flower, we are to its chloroform recovery portion
Position carries out the extraction separation of system and purified, and carries out screening active ingredients using existing Research foundation, to find active high, poison
The ACEI active components of Small side effects.By present study, fulvoushair honeysuckle flower plant resources can be further developed, is new
Lead compound is found in the development of antihypertensive drugs.
The content of the invention
To achieve the above object, the present invention provides a kind of fulvoushair honeysuckle flower moderate resistance hypertensin conversion enzyme activity composition
Screening technique, filters out cypress biflavone and apiolin with high activity, solves problems of the prior art.
The technical solution adopted in the present invention is, a kind of fulvoushair honeysuckle flower moderate resistance hypertensin conversion enzyme activity composition
Screening technique, is specifically followed the steps below：
Step 1, raw material fulvoushair honeysuckle flower crushed, extracted 3 times with alcohol reflux, merge extract solution, reclaim ethanol extremely
Without alcohol taste, liquid extract is obtained；
Step 2, liquid extract is diluted with water, extracted with chloroform, obtain chloroform extract；
Step 3, chloroform extract are through silica gel column chromatography, with chloroform-methanol (100:1~1:1) gradient elution is thin with silica gel
Layer chromatography instructs to merge same composition, obtains flow point 1~17；
Step 4, to above-mentioned 17 groups of flow points, active testing is carried out respectively；
The good flow point of step 5, selection activity, through silica gel column chromatography, with chloroform-methanol (60:1~8:1) gradient elution, then
Through Sephadex LH-20 gel column chromatographies, with chloroform-methanol (1:1~0:1) it is eluent；
Step 6, obtain after above-mentioned separation ursolic acid, naringenin, apiolin, cyanidenon -7-O- β-D-Glucose glycosides,
Cypress biflavone and caffeic acid.
Further, in the step 1, raw material fulvoushair honeysuckle flower is crushed to 180-220 mesh.
Further, in the step 1, extracted 3 times with the alcohol reflux of 90% concentration, for the first time with 12 times of raw material
Ethanol extract 2 hours, second with the ethanol extractions 2 hours of 9 times of raw material, for the third time with the ethanol of 7 times of raw material
Extract 1.5 hours.
Further, in the step 4, active testing method of testing is as follows：By 8-12mM substrate hippuroyl-group ammonia
Acyl-leucine and ACE react 45min in 37 DEG C of water-bath, with 1.2M hydrochloric acid terminating reaction, then use chloroform extractive reaction
The hippuric acid of generation, it is soluble in water after chloroform is evaporated, then the suction of product hippuric acid is determined with spectrophotometer at 228nm
Shading value；Blank control, negative control and positive control are set up for each sample；Assuming that letter N, S, B are represented respectively
The absorbance of negative control, the absorbance of determination sample, the absorbance of blank control, then, sample ACE inhibiting rates %=
100% (N-S)/(N-B).
Beneficial effects of the present invention：A kind of sieve of the fulvoushair honeysuckle flower moderate resistance hypertensin conversion enzyme activity composition proposed
Choosing method, can be extracted and be separated to the active ingredient of fulvoushair honeysuckle flower, systematic research fulvoushair honeysuckle flower active component
Chemical Diversity, explore and excavate fulvoushair honeysuckle flower antiangiotensin invertase activity composition, and for research and development
New antiangiotensin invertase medicine provides scientific basis and theoretical foundation.
Brief description of the drawings
In order to illustrate more clearly about the embodiment of the present invention or technical scheme of the prior art, below will be to embodiment or existing
There is the accompanying drawing used required in technology description to be briefly described, it should be apparent that, drawings in the following description are only this
Some embodiments of invention, for those of ordinary skill in the art, on the premise of not paying creative work, can be with
Other accompanying drawings are obtained according to these accompanying drawings.
Fig. 1 is the flow chart of the present invention.
Embodiment
Below in conjunction with the embodiment of the present invention, the technical scheme in the embodiment of the present invention is clearly and completely retouched
State, it is clear that described embodiment is only a part of embodiment of the invention, rather than whole embodiments.Based on the present invention
In embodiment, the every other implementation that those of ordinary skill in the art are obtained under the premise of creative work is not made
Example, belongs to the scope of protection of the invention.
A kind of screening technique of fulvoushair honeysuckle flower moderate resistance hypertensin conversion enzyme activity composition, specifically according to following steps
Carry out：
Step 1, raw material fulvoushair honeysuckle flower is crushed to 200 mesh, extracts 3 with the alcohol reflux of 90% concentration at normal temperatures
It is secondary, extracted 2 hours with the ethanol of 12 times of raw material for the first time, second of the ethanol with 9 times of raw material is extracted 2 hours, the
The ethanol of three use, 7 times of raw material is extracted 1.5 hours, merges extract solution, is reclaimed ethanol to without alcohol taste, is obtained liquid extract；
Step 2, liquid extract is diluted with water, respectively with petroleum ether, chloroform and extracting n-butyl alcohol, respectively obtains petroleum ether and carry
Take thing, chloroform extract, n-butanol extract；
Find that chloroform extract activity is higher because being screened through Preliminary activation, the no activity of other two parts, therefore subsequently only
Chloroform extract is studied.
Step 3, chloroform extract are through silica gel column chromatography, with chloroform-methanol (100:1~1:1) gradient elution is thin with silica gel
Layer chromatography instructs to merge same composition, obtains flow point 1~17；
Step 4, to above-mentioned 17 groups of flow points, active testing is carried out respectively, method of testing is as follows：8-12mM substrate horse is urinated
Acyl-histidyl--leucine (HHL) and ACE react 45min in 37 DEG C of water-bath, with 1.2M hydrochloric acid terminating reaction, then use
The hippuric acid of chloroform extractive reaction generation, it is soluble in water after chloroform is evaporated, then production is determined at 228nm with spectrophotometer
The absorbance of product hippuric acid；Blank control, negative control and positive control are set up for each sample.Assuming that letter N,
S, B represent the absorbance of negative control, the absorbance of determination sample, the absorbance of blank control respectively, then, sample
ACE inhibiting rates %=100% (N-S)/(N-B).7,9,11,15 flow points activity is found after tested preferably.
Step 5, flow point 7 are through silica gel column chromatography, with chloroform-methanol (60:1~30:1) gradient elution, then through Sephadex
LH-20 gel column chromatographies, with chloroform-methanol (1:1) it is eluent；Flow point 9 is through silica gel column chromatography, with chloroform-methanol
(50:1~20:1) gradient elution, then through Sephadex LH-20 gel column chromatographies, with chloroform-methanol (1:1) washed for eluant, eluent
It is de-；Flow point 11 is through silica gel column chromatography, with chloroform-methanol (30:1~10:1) gradient elution, then through Sephadex LH-20 gels
Column chromatography, with chloroform-methanol (1:3) it is eluent；Flow point 15 is through silica gel column chromatography, with chloroform-methanol (20:1~8:1)
Gradient elution, then through Sephadex LH-20 gel column chromatographies, using methanol as eluent；
Step 6, ursolic acid (1), naringenin (2), apiolin (3), cyanidenon -7-O- β-D- are obtained after above-mentioned separation
The monomeric compounds such as glucoside (4), cypress biflavone (5) and caffeic acid (6), through active testing.Cypress biflavone (5) display is stronger
ACE inhibitory activity (during 100 μM/mL concentration, inhibiting rate be 86%), apiolin show moderate strength ACE inhibitory activity
(during 200 μM/mL concentration, 62%) inhibiting rate is.The content of cypress biflavone and apiolin in fulvoushair honeysuckle flower is higher.
The molecular structural formula of wherein ursolic acid is：
The molecular structural formula of naringenin is：
The molecular structural formula of apiolin is：
The molecular structural formula of cyanidenon -7-O- β-D-Glucose glycosides is：
The molecular structural formula of cypress biflavone is：
Caffeinic molecular structural formula is：
The foregoing is merely illustrative of the preferred embodiments of the present invention, is not intended to limit the scope of the present invention.It is all
Any modification, equivalent substitution and improvements made within the spirit and principles in the present invention etc., are all contained in protection scope of the present invention
It is interior.
Claims (4)
1. a kind of screening technique of fulvoushair honeysuckle flower moderate resistance hypertensin conversion enzyme activity composition, it is characterised in that specifically press
Carried out according to following steps：
Step 1, raw material fulvoushair honeysuckle flower crushed, extracted 3 times with alcohol reflux, merge extract solution, reclaim ethanol to without alcohol
Taste, obtains liquid extract；
Step 2, liquid extract is diluted with water, extracted with chloroform, obtain chloroform extract；
Step 3, chloroform extract are through silica gel column chromatography, with chloroform-methanol (100:1~1:1) gradient elution, with silica gel thin-layer chromatography
Spectrum instructs to merge same composition, obtains flow point 1~17；
Step 4, to above-mentioned 17 groups of flow points, active testing is carried out respectively；
The good flow point of step 5, selection activity, through silica gel column chromatography, with chloroform-methanol (60:1~8:1) gradient elution, then pass through
Sephadex LH-20 gel column chromatographies, with chloroform-methanol (1:1~0:1) it is eluent；
Step 6, ursolic acid, naringenin, apiolin, cyanidenon -7-O- β-D-Glucose glycosides, Bai Shuan are obtained after above-mentioned separation
Flavones and caffeic acid.
2. the screening technique of fulvoushair honeysuckle flower moderate resistance hypertensin conversion enzyme activity composition according to claim 1, its
It is characterised by, in the step 1, raw material fulvoushair honeysuckle flower is crushed to 180-220 mesh.
3. the screening technique of fulvoushair honeysuckle flower moderate resistance hypertensin conversion enzyme activity composition according to claim 1, its
It is characterised by, in the step 1, is extracted 3 times, carried for the first time with the ethanol of 12 times of raw material with the alcohol reflux of 90% concentration
Take 2 hours, second of the ethanol with 9 times of raw material is extracted 2 hours, extracts 1.5 with the ethanol of 7 times of raw material for the third time small
When.
4. the screening technique of fulvoushair honeysuckle flower moderate resistance hypertensin conversion enzyme activity composition according to claim 1, its
It is characterised by, in the step 4,
Active testing method of testing is as follows：By 8-12mM substrate hippuroyl-histidyl--leucine and ACE in 37 DEG C of water-bath
Middle reaction 45min, with 1.2M hydrochloric acid terminating reaction, the hippuric acid then generated with chloroform extractive reaction, after chloroform is evaporated,
It is soluble in water, then the absorbance of product hippuric acid is determined with spectrophotometer at 228nm；Set up for each sample
Blank control, negative control and positive control；Assuming that letter N, S, B represent the absorbance of negative control, determination sample respectively
Absorbance, the absorbance of blank control, then, sample ACE inhibiting rates %=100% (N-S)/(N-B).
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108409533A (en) * | 2018-04-11 | 2018-08-17 | 江苏省中国科学院植物研究所 | A kind of largeflower-like honeysuckle flower diterpene-kind compound and preparation method thereof and anti-agriculture fungi purposes |
| CN110772555A (en) * | 2019-12-02 | 2020-02-11 | 贵州中医药大学 | Application of different solvent extracts of Lonicera fulvidraco in pharmacy and preparation method thereof |
| CN110974834A (en) * | 2019-12-02 | 2020-04-10 | 贵州中医药大学 | Application of Lonicera fulvidraco acid hydrolysate in pharmacy and preparation method thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106511327A (en) * | 2016-09-29 | 2017-03-22 | 滨州医学院 | Application of ACEI active ingredient in Lonicera edulis Turcz in preparation of anti-hypertension drugs |
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2017
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106511327A (en) * | 2016-09-29 | 2017-03-22 | 滨州医学院 | Application of ACEI active ingredient in Lonicera edulis Turcz in preparation of anti-hypertension drugs |
Non-Patent Citations (1)
| Title |
|---|
| 李洪娟: "钮子瓜和袋花忍冬的化学成分研究", 《中国优秀博硕士学位论文全文数据库 (硕士)医药卫生科技辑》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108409533A (en) * | 2018-04-11 | 2018-08-17 | 江苏省中国科学院植物研究所 | A kind of largeflower-like honeysuckle flower diterpene-kind compound and preparation method thereof and anti-agriculture fungi purposes |
| CN108409533B (en) * | 2018-04-11 | 2021-02-05 | 江苏省中国科学院植物研究所 | Lonicera macranthoides diterpenoid compound, preparation method thereof and agricultural fungus resisting application |
| CN110772555A (en) * | 2019-12-02 | 2020-02-11 | 贵州中医药大学 | Application of different solvent extracts of Lonicera fulvidraco in pharmacy and preparation method thereof |
| CN110974834A (en) * | 2019-12-02 | 2020-04-10 | 贵州中医药大学 | Application of Lonicera fulvidraco acid hydrolysate in pharmacy and preparation method thereof |
| CN110772555B (en) * | 2019-12-02 | 2021-10-12 | 贵州中医药大学 | Application of different solvent extracts of Lonicera fulvidraco in pharmacy and preparation method thereof |
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Application publication date: 20171107 |